Palladium-Catalyzed Aminosulfonylation of <i>ortho</i>-Iodoanilines with the Insertion of Sulfur Dioxide for the Synthesis of 3,4-Dihydro-benzothiadiazine 1,1-Dioxides
Zhenjie Qi, Simiaomiao Wen, Hao Li, Shuai Liu, Dongfang Jiang
Abstract
A simple and efficient Pd-catalyzed oxidative cyclization system is developed for the chemo- and regioselective synthesis of 3,4-dihydro-benzothiadiazine 1,1-dioxides, which are formed through aminosulfonylation of ortho -iodoanilines with SO 2 . DABSO is utilized as the source of SO 2, and the organic compound O 2 acts as an oxidant. This direct C–S, S–N, and C–N functionalization is highly efficient, and broad functional group tolerance is observed, resulting in moderate to excellent yields of 3,4-dihydro-benzothiadiazine 1,1-dioxides. Furthermore, this method is amenable to gram-scale synthesis.
Topics & Concepts
BenzothiadiazineChemistryRegioselectivityCatalysisSulfurPalladiumCombinatorial chemistryFunctional groupSulfur dioxideMedicinal chemistryOrganic chemistryPolymerSulfur-Based Synthesis TechniquesPhenothiazines and Benzothiazines Synthesis and ActivitiesCatalytic C–H Functionalization Methods